The biggest idiot in music history is, famously, the guy who passed up the chance to sign The Beatles. The second biggest has to be the guy who decided that “Ice Ice Baby” would make a terrific b-side for Vanilla Ice’s first single, “Play That Funky Music”.

“Ice Ice Baby” is a load-bearing beam of 90s pop culture. It appears on every Best Song of the 90s list. It’s on every Worst Song of the 90s list. I don’t think anyone would deny that it is an insanely, infectiously catchy tune, even if we disagree about whether it’s any good.

“Play That Funky Music”, re-released after “Ice Ice Baby” went mega-global, is not as good. For me, the most interesting thing about the song is that it has this weird glockenspiel effect in the background that sounds exactly like a guy snoring. Maybe the sound engineer fell asleep at the mixing board. It serves as a reminder of how nothing the beat is, and how Vanilla’s flow is clunky and lumbering.

Of course, the full line of the chorus is “play that funky music, white boy,” as it was in the original Wild Cherry song. It feels egregious now in 2021, when there’s such intense debate about cultural appropriation. And hey, it was egregious in 1991 as well. White people have a long and shameful history of stealing Black culture and repackaging it as something much lamer. We’ve been doing it since Elvis, if not before.

Vanilla seems aware of this in the video. It’s almost like he’s hanging a lampshade on it, dragging our attention to the fact that he is a white guy just straight up hijacking Black culture. The fact that he’s dressed so white, playing to an audience so white, performing in an idiom so white, just makes you break out in a full-body cringe.

But was there more to Vanilla Ice than this?

Last year, Vanilla Ice did a long autobiographical interview with The Ringer, in which he told the whole story of his rise and fall. There’s a lot of obvious rewriting. Like, he tries to reclaim one of hip-hop’s most infamous anecdotes (Suge Knight hung him over a balcony until he signed away a cut of the “Ice Ice Baby” money) to make himself sound like less of a sucker.

But it’s interesting to dig deep into the real story behind his ascent. As he tells it, he was a poor kid from a crappy background, who became a hardcore hip-hop fan in his teens, learning to rap and dance at the heart of the nascent Houston scene in the late 80s. The “go white boy, go white boy, go” part of “Play That Funky Music” is something he claims that Black audiences genuinely chanted at him.

No less a figure than Public Enemy’s Chuck D wanted to sign Vanilla Ice, which is admittedly one hell of an endorsement (although Chuck could easily have been planning to use him to prove a point.) Vanilla almost went to Def Jam, which could possibly have seen him take more of an Eminem path. Eminem got away with a lot of things because he had Dr Dre behind him. What might have happened if someone like Chuck D had contributed a verse to “Play That Funky Music”?

But that didn’t happen. Instead, Vanilla borrowed a pair of Hammer’s parachute pants and Joan Collins’ shoulder pads and became the punchline to a joke. Did you hear the one about the white rapper? A lot of that is his own fault. No one forced him to make his extremely bad vanity movie, Cool as Ice. Everything came crashing down during a vicious Arsenio Hall interview during which, as The Ringer puts it, “you can see his career leave his body.”

Could he have been something more? Could he have been a serious rapper? No, probably not, but I found myself watching the original video for the small-label release of “Play That Funky Music”. Instead of a packed arena, this video plays out in the middle of the street after a show.

It’s the same song with the same guy snoring in the back of the mix. But there’s so much more energy and optimism in it. The video cuts to live audio for Vanilla to freestyle his terrible rhyme:

Now you're amazed by the VIP posse
Steppin' so hard like a German Nazi

It works better here than it does in the big-budget video. His goofy smile helps to sell it.

Elsewhere in the charts

• Bart Simpson enjoys his third and final week at the top with the Michael Jackson-penned “Do the Bartman”. Nancy Cartwright probably enjoys a better reputation in hip-hop than Vanilla Ice.

• A reissue of Madonna’s “Crazy for You” almost goes straight to the top. This song was originally recorded for a movie called Vision Quest that nobody has ever seen.

• The top 100 is a seething mess of white label dance tracks, which is what was really happening in music around this time. Occasionally would would bubble into mainstream consciousness, like this week’s number 10, “Move Your Body” by Xpansions.

• “Here Comes The Hammer” yells another one-hit-wonder. MC Hammer actually will eventually have another hit with that Addams Family song. Vanilla Ice will soon do the same with Ninja Turtles.

• I remember my older brothers talking in hushed tones about a “Black heavy metal band” like it was a two-headed dog. Living Colour were awesome and did funk-rock better than most people. I love “Love Rears Its Ugly Head”.

• Slim pickings on this week’s Top of the Pops, which was mostly videos. The lucky study audience got to see N-Joi, Jesus Jones and Massive Attack.

Next week

How can a pair of jeans help sell a million records? It happened a lot in the 90s. Even leftie bands like The Clash got some of that sweet Levi’s money with “Should I Stay or Should I Go”.